PREPARATION OF ALKYL SILYL ACETALS FROM CARBOXYLIC ESTERS WITH TERT-BUTYLDIMETHYLSILYLDIHALOMETHYLLITHIUM - 1,3-REARRANGEMENT OF SILYL GROUP FROM CARBON TO OXYGEN

被引:18
作者
SHINOKUBO, H [1 ]
OSHIMA, K [1 ]
UTIMOTO, K [1 ]
机构
[1] KYOTO UNIV,FAC ENGN,DIV MAT CHEM,SAKYO KU,KYOTO 60601,JAPAN
关键词
D O I
10.1246/cl.1995.461
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Treatment of ethyl benzoate or isopropyl formate with tert-butyldimethylsilyldibromomethyllithium gave alkyl silyl mixed acetal via 1,3-rearrangement of silyl group from carbon to oxygen. The reaction of the mixed acetals with allylsilane in the presence of Lewis acid afforded allylated ethers.
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页码:461 / 462
页数:2
相关论文
共 8 条
[1]   ASYMMETRIC-SYNTHESIS VIA ACETAL TEMPLATES .3. ON THE STEREOCHEMISTRY OBSERVED IN THE CYCLIZATION OF CHIRAL ACETALS OF POLYOLEFINIC ALDEHYDES - FORMATION OF OPTICALLY-ACTIVE HOMOALLYLIC ALCOHOLS [J].
BARTLETT, PA ;
JOHNSON, WS ;
ELLIOTT, JD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (07) :2088-2089
[2]   CHEMISTRY OF ORGANOSILICON COMPOUNDS .91. ALLYLSILANES AS SYNTHETIC INTERMEDIATES .2. SYNTHESES OF HOMOALLYL ETHERS FROM ALLYLSILANES AND ACETALS PROMOTED BY TITANIUM TETRACHLORIDE [J].
HOSOMI, A ;
ENDO, M ;
SAKURAI, H .
CHEMISTRY LETTERS, 1976, (09) :941-942
[3]   HIGHLY SELECTIVE ACETAL CLEAVAGE USING NEW ORGANOALUMINUM REAGENTS [J].
ISHIHARA, K ;
HANAKI, N ;
YAMAMOTO, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (18) :7074-7075
[4]   1ST GENERAL-SYNTHESIS OF MONOSILYL ACETALS - TRIMETHYLSILYL TRAPPING OF THE INTERMEDIATE IN DIBALH REDUCTION OF CARBOXYLIC-ACID ESTERS USING TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE [J].
KIYOOKA, S ;
SHIROUCHI, M ;
KANEKO, Y .
TETRAHEDRON LETTERS, 1993, 34 (09) :1491-1494
[5]  
MUKAIYAMA T, 1987, SYNTHESIS-STUTTGART, P1043
[6]   AN EFFICIENT AND CONVENIENT METHOD FOR THE ASYMMETRIC ALLYLATION OF ALDEHYDES WITH ALLYLTRIMETHYLSILANE CATALYZED BY DIPHENYLBORYL TRIFLATE [J].
MUKAIYAMA, T ;
OHSHIMA, M ;
MIYOSHI, N .
CHEMISTRY LETTERS, 1987, (06) :1121-1124
[7]   EVIDENCE FOR AN OXOCARBENIUM ION INTERMEDIATE IN LEWIS-ACID MEDIATED REACTIONS OF ACYCLIC ACETALS [J].
SAMMAKIA, T ;
SMITH, RS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (17) :7915-7916
[8]   TERT-BUTYLDIMETHYLSILYLDICHLOROMETHYLLITHIUM AS A DICHLOROMETHYLENE DIANION SYNTHON - 1,3-REARRANGEMENT OF SILYL GROUP FROM CARBON TO OXIDE [J].
SHINOKUBO, H ;
MIURA, K ;
OSHIMA, K ;
UTIMOTO, K .
TETRAHEDRON LETTERS, 1993, 34 (12) :1951-1954